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Enamine
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<p>An enamine is an <a href="/facts/Unsaturated_compound/tde2C216">unsaturated compound</a> derived by the condensation of an <a href="/facts/Aldehyde/xSIRkW03">aldehyde</a> or <a href="/facts/Ketone/BqQXpLo4">ketone</a> with a secondary <a href="/facts/Amine/JvfYJfP6">amine</a>. Enamines are versatile intermediates. </p> <p>The word "enamine" is derived from the affix <i>en</i>-, used as the suffix of <a href="/facts/Alkene/RtYcS6kU">alkene</a>, and the root <i>amine</i>. This can be compared with <a href="/facts/Enol/aySJNbQx">enol</a>, which is a functional group containing both alkene (<i>en</i>-) and <a href="/facts/Alcohol_(chemistry)/Y0SCTDkh">alcohol</a> (-<i>ol</i>). Enamines are considered to be nitrogen analogs of enols. </p><p>If one or both of the nitrogen substituents is a hydrogen atom it is the <a href="/facts/Tautomer/ucdXGP9C">tautomeric</a> form of an <a href="/facts/Imine/yK72z07j">imine</a>. This usually will rearrange to the imine; however there are several exceptions (such as <a href="/facts/Aniline/eFXck1Rj">aniline</a>). The enamine-imine tautomerism may be considered analogous to the <a href="/facts/Keto-enol_tautomerism/aySJNbQx">keto-enol tautomerism</a>. In both cases, a hydrogen atom switches its location between the heteroatom (oxygen or nitrogen) and the second carbon atom. </p><p>Enamines are both good nucleophiles and good bases. Their behavior as carbon-based nucleophiles is explained with reference to the following resonance structures. </p>